This invention relates to novel N-[(pyridyl or pyrimidyl)aminocarbonyl]arylsulfonamides, to herbicidal compositions containing them and to methods of using them to control the growth of undesired vegetation.
New compounds effective for controlling the growth of undesired vegetation are in constant demand. In the most common situation, such compounds are sought to selectively control the growth of weeds in useful crops such as cotton, rice, corn, wheat and soybeans, to name a few. Unchecked weed growth in such crops can cause significant losses, reducing profit to the farmer and increasing costs to the consumer. In other situations, herbicides are desired which will control all plant growth. Examples of areas in which complete control of all vegetation is desired are areas around fuel storage tanks, ammunition depots and industrial storage areas. These are many products commercially available for these purposes, but the search continues for products which are more effective, less costly and environmentally safe.
A number of different types of N-[(heterocyclic)aminocarbonyl]arylsulfonamides are known as herbicides. Two of the first patents to issue on such compounds are U.S. Pat. Nos. 4,169,719 and 4,127,405, issued on Oct. 2, 1979 and Nov. 28, 1978, respectively. These patents disclose compounds of the general formula ##STR1## where R.sub.1 can be optionally substituted benzene, thiophene, pyrrole, furan or unsubstituted naphthalene,
and Y is N or CH. PA1 R.sub.2 and R.sub.3 are independently H, halogen, C.sub.1 -C.sub.4 alkyl, C.sub.1 -C.sub.4 alkoxy, etc.; or PA1 Q and R.sub.2 together can also form a 2-4 membered carbon chain, which may still contain an oxygen or sulfur atom, or the group NR.sub.5 ; PA1 R.sub.1 is H, halogen, nitro or a group ##STR5## R.sub.4 is H, halogen, C.sub.1 -C.sub.4 alkyl, methoxy, nitro or trifluoromethyl; PA1 Z is O or S; PA1 R.sub.5 is H, C.sub.1 -C.sub.4 alkyl or C.sub.3 -C.sub.4 alkenyl. PA1 R.sub.1 is NO.sub.2, Cl, Br, CF.sub.3, C.sub.1 -C.sub.3 alkyl, C.sub.1 -C.sub.2 alkyl substituted with OCH.sub.3 or OC.sub.2 H.sub.5, CO.sub.2 R.sub.9, SO.sub.2 N(CH.sub.3)R.sub.10, S(O).sub.n R.sub.11, S(O).sub.n CF.sub.2 H, S(O).sub.n CF.sub.3, OR.sub.12, OSO.sub.2 R.sub.11, CH.sub.2 CH.sub.2 Cl, C(O)R.sub.25, ##STR8## R.sub.2 is H, C.sub.1 -C.sub.2 alkyl, C.sub.1 -C.sub.2 alkoxy, C.sub.1 -C.sub.2 alkylthio, C.sub.1 -C.sub.2 alkylsulfinyl, C.sub.1 -C.sub.2 alkylsulfonyl, C.sub.1 -C.sub.2 haloalkyl or halogen; PA1 R.sub.3 is Cl, SO.sub.2 CH.sub.3, SO.sub.2 N(CH.sub.3).sub.2, OCH.sub.3, NO.sub.2 or N(CH.sub.3).sub.2 ; PA1 R.sub.4 is H or CH.sub.3 ; PA1 R.sub.5 is H or C.sub.1 -C.sub.3 alkyl; PA1 R.sub.6 is CO.sub.2 R.sub.9, S(O).sub.n R.sub.11, C.sub.1 -C.sub.3 alkyl, Cl, Br or SO.sub.2 N(CH.sub.3).sub.2 ; PA1 R.sub.7 is S(O).sub.n R.sub.11, OSO.sub.2 R.sub.11, C.sub.1 -C.sub.3 alkyl, C.sub.1 -C.sub.3 alkoxy or Cl; PA1 R.sub.8 is C.sub.1 -C.sub.3 alkyl; PA1 R.sub.9 is C.sub.1 -C.sub.3 alkyl, CH.sub.2 CH.dbd.CH.sub.2, CH.sub.2 CH.sub.2 Cl or CH.sub.2 CH.sub.2 OCH.sub.3 ; PA1 R.sub.10 is C.sub.1 -C.sub.3 alkyl or OCH.sub.3 ; PA1 R.sub.11 is C.sub.1 -C.sub.3 alkyl; PA1 R.sub.12 is C.sub.1 -C.sub.3 alkyl, CH.sub.2 CH.sub.2 OCH.sub.3, C.sub.3 -C.sub.4 alkenyl, C.sub.3 -C.sub.4 alkynyl or C.sub.1 -C.sub.3 alkyl substituted with 1-3 atoms of Cl or F, or with 1 Br; PA1 R.sub.13 is H or CH.sub.3 ; PA1 m is 0 or 1; PA1 n is 0, 1 or 2; PA1 Q is O, S, SO or SO.sub.2 ; ##STR9## W is F, CH.sub.3, OCH.sub.3, CN, CO.sub.2 CH.sub.3, CO.sub.2 C.sub.2 H.sub.5, NO.sub.2, C(O)R.sub.25, S(O)R.sub.11, SO.sub.2 R.sub.11 or CONR.sub.14 R.sub.15 ; PA1 R.sub.14 and R.sub.15 are independently H or CH.sub.3 ; PA1 X is CH.sub.3, OCH.sub.3, OC.sub.2 H.sub.5, CH.sub.2 OCH.sub.3, Cl, CH.sub.2 OH, NHCH.sub.3 or N(CH.sub.3).sub.2 ; PA1 Y is CH.sub.3, OCH.sub.3, OC.sub.2 H.sub.5 or Cl; PA1 Z is CH or N; PA1 p is 0 or 1; PA1 Q.sub.1 is O, NCH.sub.3 or CH.sub.2 ; PA1 Q.sub.2 is O, NCH.sub.3 or CH.sub.2 ; PA1 Q.sub.3 is O, SO or SO.sub.2 ; PA1 R.sub.16 is H, Cl, Br, F, CH.sub.3, OCH.sub.3, SCH.sub.3 or CF.sub.3 ; PA1 R.sub.17 is H, C.sub.1 -C.sub.5 alkyl, C.sub.2 -C.sub.3 alkoxycarbonyl, C.sub.1 -C.sub.3 alkyl substituted with 1-3 halogen atoms selected from 0-3 F, 0-3 Cl and 0-1 Br, C.sub.2 -C.sub.4 alkyl substituted with OCH.sub.3, C.sub.3 -C.sub.4 alkenyl, C.sub.3 -C.sub.4 alkynyl or benzyl; PA1 R.sub.18 is H or C.sub.1 -C.sub.2 alkyl; PA1 R.sub.19 is H, C.sub.1 -C.sub.3 alkyl, CH.sub.2 CH.dbd.CH.sub.2 or phenyl; PA1 R.sub.20 is C.sub.1 -C.sub.3 alkyl, F, Cl, Br, NO.sub.2, CO.sub.2 R.sub.9, SO.sub.2 N(CH.sub.3)R.sub.10, SO.sub.2 R.sub.11, OCF.sub.2 H or phenyl; PA1 R.sub.21 is H, Cl or CH.sub.3 ; PA1 R.sub.22 is H or C.sub.1 -C.sub.3 alkyl; PA1 R.sub.23 and R.sub.24 are independently H or Cl; and PA1 R.sub.25 is H or C.sub.1 -C.sub.2 alkyl; PA1 (1) X and Y cannot simultaneously be Cl; PA1 (2) when either X or Y is Cl, then Z is CH; PA1 (3) when X and Y are both CH.sub.3 and Z is CH, then W is other than NO.sub.2 ; PA1 (4) when Z is N, then Q.sub.3 is SO or SO.sub.2 ; and PA1 (5) when J is J-11, R.sub.19 and R.sub.20 are not both phenyl; and PA1 (6) when J is J-1, R.sub.1 is CO.sub.2 R.sub.9, A is A-1 and Z is CH, then W is other than CN. PA1 (1) Compounds of Formula I where PA1 (2) Compounds of Preferred 1 where A is A-1; PA1 (3) Compounds of Preferred 1 where A is A-2; PA1 (4) Compounds of Preferred 1 where A is A-3; PA1 (5) Compounds of Preferred 1 where A is A-4; PA1 (6) Compounds of Preferred 1 where J is J-1; PA1 (7) Compounds of Preferred 1 where J is J-2; PA1 (8) Compounds of Preferred 1 where J is J-3; PA1 (9) Compounds of Preferred 1 where J is J-4; PA1 (10) Compounds of Preferred 1 where J is J-5; PA1 (11) Compounds of Preferred 1 where J is J-6; PA1 (12) Compounds of Preferred 1 where J is J-7; PA1 (13) Compounds of Preferred 1 where J is J-8; PA1 (14) Compounds of Preferred 1 where J is J-9; PA1 (15) Compounds of Preferred 1 where J is J-10; PA1 (16) Compounds of Preferred 1 where J is J-11; PA1 (17) Compounds of Preferred 1 where J is J-12; PA1 (18) Compounds of Preferred 1 where J is J-13; PA1 (19) Compounds of Preferred 1 where J is J-14; PA1 (20) Compounds of Preferred 1 where J is J-15; PA1 (21) Compounds of Preferred 1 where J is J-16; PA1 (22) Compounds of Preferred 1 where J is J-17; PA1 (23) Compounds of Preferred 6 where PA1 (24) Compounds of Preferred 8 where R.sub.16 is H; PA1 (25) Compounds of Preferred 9 where R.sub.16 is H; PA1 (26) Compounds of Preferred 13 where R.sub.16 is H; PA1 (27) Compounds of Preferred 15 where R.sub.21 is H; PA1 (28) Compounds of Preferred 16 where R.sub.21 is H; PA1 (29) Compounds of Preferred 17 where R.sub.21 is H; PA1 (30) Compounds of Preferred 18 where R.sub.21 is H; PA1 (31) Compounds of Preferred 21 where R.sub.16 is H; PA1 (32) Compounds of Preferred 22 where R.sub.16 is H; PA1 (33) Compounds of Preferred 23 where X and Y are independently CH.sub.3 or OCH.sub.3 ; and W is CN, NO.sub.2 or CO.sub.2 CH.sub.3 ; PA1 (34) Compounds of Preferred 7 where X and Y are independently CH.sub.3 or OCH.sub.3 ; and W is CN, NO.sub.2 or CO.sub.2 CH.sub.3 ; PA1 (35) Compounds of Preferred 24 where X and Y are independently CH.sub.3 or OCH.sub.3 ; and W is CN, NO.sub.2 or CO.sub.2 CH.sub.3 ; PA1 (36) Compounds of Preferred 25 where X and Y are independently CH.sub.3 or OCH.sub.3 ; and W is CN, NO.sub.2 or CO.sub.2 CH.sub.3 ; PA1 (37) Compounds of Preferred 10 where X and Y are independently CH.sub.3 or OCH.sub.3 ; and W is CN, NO.sub.2 or CO.sub.2 CH.sub.3 ; PA1 (38) Compounds of Preferred 11 where X and Y are independently CH.sub.3 or OCH.sub.3 ; and W is CN, NO.sub.2 or CO.sub.2 CH.sub.3 ; PA1 (39) Compounds of Preferred 12 where X and Y are independently CH.sub.3 or OCH.sub.3 ; and W is CN, NO.sub.2 or CO.sub.2 CH.sub.3 ; PA1 (40) Compounds of Preferred 26 where X and Y are independently CH.sub.3 or OCH.sub.3 ; and W is CN, NO.sub.2 or CO.sub.2 CH.sub.3 ; PA1 (41) Compounds of Preferred 14 where X and Y are independently CH.sub.3 or OCH.sub.3 ; and W is CN, NO.sub.2 or CO.sub.2 CH.sub.3 ; PA1 (42) Compounds of Preferred 27 where X and Y are independently CH.sub.3 or OCH.sub.3 ; and W is CN, NO.sub.2 or CO.sub.2 CH.sub.3 ; PA1 (43) Compounds of Preferred 28 where X and Y are independently CH.sub.3 or OCH.sub.3 ; and W is CN, NO.sub.2 or CO.sub.2 CH.sub.3 ; PA1 (44) Compounds of Preferred 29 where X and Y are independently CH.sub.3 or OCH.sub.3 ; and W is CN, NO.sub.2 or CO.sub.2 CH.sub.3 ; PA1 (45) Compounds of Preferred 30 where X and Y are independently CH.sub.3 or OCH.sub.3 ; and W is CN, NO.sub.2 or CO.sub.2 CH.sub.3 ; PA1 (46) Compounds of Preferred 19 where X and Y are independently CH.sub.3 or OCH.sub.3 ; and W is CN, NO.sub.2 or CO.sub.2 CH.sub.3 ; PA1 (47) Compounds of Preferred 20 where X and Y are independently CH.sub.3 or OCH.sub.3 ; and W is CN, NO.sub.2 or CO.sub.2 CH.sub.3 ; PA1 (48) Compounds of Preferred 31 where X and Y are independently CH.sub.3 or OCH.sub.3 ; and W is CN, NO.sub.2 or CO.sub.2 CH.sub.3 ; PA1 (49) Compounds of Preferred 32 where X and Y are independently CH.sub.3 or OCH.sub.3 ; and W is CN, NO.sub.2 or CO.sub.2 CH.sub.3 ; PA1 (50) Compounds of Preferred 33 where A is A-1; and Z is CH; PA1 (51) Compounds of Preferred 34 where A is A-1; and Z is CH; PA1 (52) Compounds of Preferred 35 where A is A-1; and Z is CH; PA1 (53) Compounds of Preferred 36 where A is A-1; and Z is CH; PA1 (54) Compounds of Preferred 37 where A is A-1; and Z is CH; PA1 (55) Compounds of Preferred 38 where A is A-1; and Z is CH; PA1 (56) Compounds of Preferred 39 where A is A-1; and Z is CH; PA1 (57) Compounds of Preferred 40 where A is A-1; and Z is CH; PA1 (58) Compounds of Preferred 41 where A is A-1; and Z is CH; PA1 (59) Compounds of Preferred 42 where A is A-1; and Z is CH; PA1 (60) Compounds of Preferred 43 where A is A-1; and Z is CH; PA1 (61) Compounds of Preferred 44 where A is A-1; and Z is CH; PA1 (62) Compounds of Preferred 45 where A is A-1; and Z is CH; PA1 (63) Compounds of Preferred 46 where A is A-1; and Z is CH; PA1 (64) Compounds of Preferred 47 where A is A-1; and Z is CH; PA1 (65) Compounds of Preferred 48 where A is A-1; and Z is CH; PA1 (66) Compounds of Preferred 49 where A is A-1; and Z is CH;
Subsequent patents which have issued have disclosed related compounds with different N-heterocycles. For example, U.S. Pat. No. 4,293,330, issued on Oct. 6, 1981, discloses pyridyl sulfonylureas, and U.S. Pat. No. 4,221,585, issued on Sept. 9, 1980, disclose 4-pyrimidyl sulfonylureas. Nowhere in the art has there been any indication that N-(pyridyl or pyrimidyl)sulfonylurea derivatives, in which the pyridyl or pyrimidyl moiety is substituted ortho- to the sulfonylurea bridge with an electron-withdrawing group, would exhibit high herbicidal activity.
West German patent application No. 3151450A, published 7/14/83, filed by Celamerck discloses sulfamate sulfonylureas of the following general structure. ##STR2##
European Publication No. 126,711, published 11/28/84 discloses herbicidal sulfonylureas of the formula ##STR3## where, in part, X is O, S, --NR.sub.5 --, ##STR4## --CH.dbd.CH-- or an annelated phenyl ring; Q is, inter alia, halogen, C.sub.1 -C.sub.4 alkyl, nitro, C.sub.1 -C.sub.4 alkoxycarbonyl, C.sub.1 -C.sub.4 alkylsulfonyl;